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A Natural Diels-Alder Biocatalyst Enables Efficient [4+2] Cycloaddition Under Harsh Reaction Conditions

Lookup NU author(s): Dr James StachORCiD, Professor Paul RaceORCiD

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This is the authors' accepted manuscript of an article that has been published in its final definitive form by Wiley Blackwell, 2019.

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Abstract

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimCarbon-carbon bond formation is a fundamental transformation in both synthetic chemistry and biosynthesis. Enzymes catalyze such reactions with exquisite selectivity which often cannot be achieved using non-biological methods but may suffer from an intolerance of high temperature and the presence of organic solvents limiting their applications. Here we report the thermodynamic and kinetic stability of the β-barrel natural Diels-Alderase AbyU, which catalyzes formation of the spirotetronate core of the antimicrobial natural product abyssomicin C, with creation of 3 new asymmetric centers. This enzyme is shown to catalyze [4+2] cycloadditions at elevated temperature (up to 65 °C), and in the presence of organic solvents (MeOH, CH3CN and DMSO) and the chemical denaturant guanidinium hydrochloride, revealing that AbyU has potential widespread value as a biocatalyst.

Publication metadata

Author(s): Marsh CO, Lees NR, Han L-C, Byrne MJ, Mbatha SZ, Maschio L, Pagden-Ratcliffe S, Duke PW, Stach JEM, Curnow P, Willis CL, Race PR

Publication type: Article

Publication status: Published

Journal: ChemCatChem

Year: 2019

Volume: 11

Issue: 20

Pages: 5027-5031

Print publication date: 01/10/2019

Online publication date: 25/08/2019

Acceptance date: 21/08/2019

Date deposited: 07/11/2019

ISSN (print): 1867-3880

ISSN (electronic): 1867-3899

Publisher: Wiley Blackwell

URL: https://doi.org/10.1002/cctc.201901285

DOI: 10.1002/cctc.201901285

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